The Top 10 Mistakes I’ve Made in My First Two Years as a Solopreneur

Jordan Gross

6. I stopped cooking my own dinner.

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I was wearing a beautiful blue suit with a subtle plaid design. My hair was perfectly combed, my facial hair was cleanly shaven, and my shoes were neatly polished. But my hands — my hands were covered in raw meat.

I was 23-years old, and I was in a management program for a large restaurant group in the heart of New York City. We may not always associate restaurant managers with glam and glitz, but this was the real deal. Six-figure salary, apartment on Park Avenue in the heart of New York City, conversations with celebrity guests. On paper, it seemed like a dream. But in reality, it wasn’t my dream.

Back to the raw meat. In fairness, I was wearing gloves. I was learning how to be the closing manager that night. It’s a task that most often requires staying up until at least 2am, making sure all employees were happy, and taking inventory of all leftover food products. This inventory was to be updated in a spreadsheet and sent to the entire company.

So, after counting up steaks and chops in the meat freezer, I went to plug in some numbers and send an email. But the office door was locked. No way to get in. In that moment, I started to laugh and think to myself, “what in the world am I doing at this kind of job.”

I quit the next day.

After quitting, I had to decide what was next. I had been listening to a lot of personal development podcasts, and I was reading a lot of similar kinds of books, and I knew I had to pursue something that I was more passionate about. I decided to lightly search for jobs, and in the meantime, self-publish a book about morning routines. This book was the beginning of my solopreneurial journey.

It’s been a little over two years since that book came out, and I am in a place where I can confidently say there is no turning back. There is no more light job searching. Two books, two TEDx talks, and hundreds of articles later, I am slowly but surely becoming one of those people I used to listen to on personal growth podcasts.

But my journey to this has been far from perfect. Quite the opposite actually. It has been one zig-zagged, helter-skelter type of story of mistakes, some key wins, and a lot more mistakes and failures along the way. I wanted to share some of those with you. Not necessarily so that you don’t make the same ones that I did, because that is truly part of the joy of the process, but so that you realize that these mistakes are not the end of the world. You will battle through. Below are ten of mine.

1. I had no plan

I quit my job on an absolute whim. I had nothing set up going forward. I had no other means of income. I was fortunate enough to have money saved and parents who were always going to love and support me, but other than that, I had no real prospects. Just some paragraphs in a word document that I turned into my first book.

I wouldn’t recommend not having a plan to somebody looking to start a solopreneurial or entrepreneurial venture. But it depends on your appetite for risk and your relationship with uncertainty. I was in as uncertain a position as could be. But I thrived under those circumstances. It’s up to you to know what kind of person you are.

2. I took too many off days

I remember the 2018 World Cup was being played in my first few months on my own. I figured because I was on my schedule, I could watch a few games, and make up the time another day. But that didn’t happen. I kept taking off and then not making up the time. I convinced myself that I was watching for enjoyment, and enjoyment was part of my core values. It was all hogwash.

I am not one to promote no off days. I value sleep, and I value resetting and recharging. But I know that too many of these days piled up on top of one another will lead to inefficiency and a lack of output. That is exactly how I felt.

3. I said yes to everything

I promised myself that I was going to be a yes man. There was nothing unrelated to my future pursuits. There was nothing I wouldn’t be willing to learn or talk about with others. At first, this was cool. I had conversations and learned about things that I never thought I would. Cryptocurrency, construction businesses, real estate investing. But after a little bit, saying yes to things that didn’t relate to my journey started to block time I could be spending doing other things.

Being a yes person is fun and exciting. You certainly do get to learn, and you have many stories to tell. But saying yes to absolutely everything gets exhausting very quickly. When you try to please everyone, you end up pleasing no one, especially yourself.

4. I was overly spontaneous

Not only did I say yes to everything, severely imposing upon valuable time, but also, I didn’t follow a schedule for a while. I fell too in love with the free rein I had as my own boss, and I literally believed that meant I never needed to stick to anything I planned to do. But this is how you create bad habits. This led me to days where I didn’t get anything done, weeks where it felt like I made no progress.

The beauty of being an entrepreneur and setting your own schedule is that it is yours. Nobody can tell you otherwise. But you still need to have one, or else you become far too disorganized. Spontaneity can be great for diversifying your experiences, but too much of it in business pursuits will lead to a lack of order and direction.

5. I focused too much on the short-term

Like I said, patience is essential. I wanted to get started immediately, and I wanted to see results immediately. I gravitated toward the articles about building a six-figure business in six months. I thought I could have thousands of followers in a matter of weeks. But most often, overnight successes come with years and years of foundational work.

Focusing on the long-term gives more of a sense of purpose and fulfillment. It makes everything more meaningful. It will make the joy of getting to your goal so much sweeter.

6. I stopped cooking my own dinner

This point is about the health side of the solopreneur or entrepreneurial journey. Because I was so “busy” I felt that it was okay to order in all of my meals. I didn’t have time to cook I thought. But this was terrible. My weight quickly ballooned, my blood pressure rose, and I felt like garbage.

When I started cooking my own meals and understanding what was going into my body again, I was much more productive, and my energy was at an all-time high. Cooking and eating a healthy meal were part of the work life integration and feedback loop I desired, as opposed to the work-life “balance” I thought I had.

7. I got too comfortable working from home

Something appealing to me was the lifestyle I could have as a solopreneur. I no longer had to wear a suit, comb my hair, shave my beard, or even put on shoes for that matter. I stayed in my apartment and opted for calls over meetings, because I thought the commute would waste part of my day.

But it wasn’t until I started to dress and act like I was going to work that I really began to see some progress. I got out of my pajamas, I wore jeans, I met people at coffee shops for meetings. This became far more beneficial than I could have envisioned.

8. I spread myself too thin

When I was first starting out, I just wanted to pursue every single idea I had right away. There’s no time like the present, right? Wrong. I was trying to create a non-profit, a startup, write a book, all at the same time. Plus, I was trying to run accounts across all social media platforms for each endeavor. I was putting 5–10% into each pursuit, and this led to minimal returns. It wasn’t until I narrowed my focus that I actually started to see some nice results.

It may be attractive to have the capacity to start so many different things and test out many different ideas. But it is important that you don’t do them all at the same exact time. Patience is something we often forget to stress to first time founders.

9. I was too easily convinced

I was on the phone trying to learn from others a lot in my early days and months. This meant that all different kinds of people were ultimately trying to sell me on their services. A couple hundred dollars for coaching here. A couple hundred for logo design there. I never wanted to say no to anybody or make them feel bad, so I agreed to whatever they had to offer almost always.

Just like with the point about being a yes person, it is critical to learn how to say no. When I realized that saying no would not only be beneficial to me, but also to the other person so as not to waste their time, then I began to make some wise decisions about the direction of my ventures.

10. I placed ZERO importance on money

My mindset is one in which I follow my passions and curiosities, live according to serving the world and helping others, and the money will follow. But, at first, I took this literally, and I did not care about spending or making money one bit. It had no importance to me. I didn’t care if I gave it all away and made nothing back, because I just believed that if I served others, it would follow.

But then I heard a mindset about money that shifted my perspective. It’s that money makes you more of who you really are. So, for me, the more money I can make, the more money I can use for good to help more people.

Many of these lessons are based on personality type and the situation you are currently in. For instance, some of you may want to be as spontaneous as possible because you are still in the learning phases. You haven’t fully made the leap, and that is okay. Others may need to focus on money now to satisfy basic needs. This will change the way you view your efforts.

The one thing and the most important thing to me about all of these lessons, and my first two years as a solopreneur, is that, cliché as it may be, I would not change any of it. I would make all the same mistakes. I would make all the same decisions. Because without these experiences, I would have had nothing to share with others, no lessons to have learned, and no stories to tell. Make mistakes on your pursuit. Document them. Be careful not to repeat the same ones over and over. Enjoy the imperfection.

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